What the Second Act Really Means

After years—often decades—at the helm of a business, stepping away can feel like crossing into unfamiliar territory. I’ve spoken to hundreds of owners who, after selling, realized the hardest part wasn’t the negotiations or the handoff, but what came next. The “second act”—a phase too few take seriously until it arrives.

Regret in the Rearview Mirror

A recent study by the Exit Planning Institute found that nearly 75% of owners regretted selling their business within a year. The reason? It wasn’t about the sale price or the company’s condition. Most simply felt unprepared for life after the sale—unmoored without their old routines, titles, and sense of purpose.

What I see again and again is that founders often underestimate how much their business defines them. Ask a soon-to-exit owner what’s next, and the answer is usually lighthearted: more golf, some travel, maybe just relaxing. But the reality hits differently. Without the rhythms of work and the sense of mission, that initial vacation can quickly turn into a restless void.

Where Identity and Purpose Go Missing

For so many, their introduction at a party, in the community, or at the country club always began, “I’m the founder of…” or “I’m the CEO of…” That identity doesn’t just go away when the business is sold. And when it does, it leaves a hole that’s hard to fill.

It’s also rare that owners fully understand the financial complexities ahead. Many don’t know what they don’t know, and strategies for minimizing taxes or optimizing the transition often require months—or even years—of planning. When these aren’t in place, the consequences are significant: not just for the owner, but for future generations. This lack of personal and financial planning is a big part of why, statistically, 70% of wealth disappears by the second generation, and 90% by the third.

Designing a Second Act with Meaning

One of the most valuable conversations I have with owners is about their time—how they want to spend it, and what will give it meaning. Business is rarely the end goal. For many, the business was simply a means to provide for their families and open doors to new possibilities. The second act is an opportunity to shape that meaning: whether it’s through philanthropy, mentorship, investment, or finally tackling the projects or causes that always had to wait.

When planning for an exit, it’s tempting to focus just on the numbers and logistics. But I’ve seen too many owners struggle with aimlessness or regret because they never planned for the life they’d step into after closing day. True preparation means building a vision for your second act as carefully as you built your business—and putting the structures in place to make it a reality.

A Final Thought

Wealth and opportunity don’t last by accident. It’s not a matter of being lucky, or even just being skilled. It’s about being prepared—personally and financially—for what’s next. That’s the work of the second act, and, in my view, it’s just as important as any sale you’ll ever make.

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